Crew Leader, Landscape Maintenance

Maintenance Crew Leader

DK Landscaping is hiring a working Maintenance Crew Leader to help run our lawn and landscape maintenance operation. This is a hands-on leadership role where you will work alongside the crew while also helping manage daily operations.

Responsibilities include leading mowing and maintenance routes, maintaining quality standards, making property decisions, keeping employees productive and accountable, handling routine customer issues, tracking equipment and supplies, and making sure unfinished work is documented and followed through. Schedule flexibility will be important and candidate must be open to early starts, later days, occasional Saturdays, and occasional overtime, as landscaping schedules are weather-dependent and we sometimes need to adjust hours to keep work on schedule.

We are looking for someone who is reliable, organized, honest, takes initiative, and can make decisions without constant direction from the owner. Previous lawn care, landscaping, equipment operation, or leadership experience is preferred.

Wisconsin DATCP pesticide applicator certification/license is strongly preferred, or willingness to obtain it.

This position includes 30-, 60-, and 90-day evaluations to make sure expectations are clear, progress is being made, and the role is a good fit for both sides.

There is real room for growth for the right person. If the job is done well, this position could grow into more responsibility as DK Landscaping grows. We’re looking for someone who doesn’t just want another job—we want someone who can help build the company, take ownership, train others, and potentially grow into a larger leadership role over time.

The goal is for this person to eventually know our properties and systems well enough to independently manage routes, solve normal field problems, train employees, and help run the maintenance operation without constant owner involvement.

Pay: $22.00 - $26.00 per hour

Expected hours: 30.0 – 50.0 per week

People with a criminal record are encouraged to apply

Work Location: In person